Being able to estimate tire/rubber friction is very important to tire engineers, materials developers, and pavement engineers. This is because of the need for estimating forces generated at the contact, optimizing tire and vehicle performance, and estimating tire wear. Efficient models for contact area and interfacial separation are key for accurate prediction of friction coefficient. Based on the contact mechanics and surface roughness, various models were developed that can predict real area of contact and penetration depth/interfacial separation. In the present work, we intend to compare the analytical contact mechanics models using experimental results and numerical analysis. Nano-indentation experiments are performed on the rubber compound to obtain penetration depth data. A finite element model of a rubber block in contact with a rough surface was developed and validated using the nano-indentation experimental data. Results for different operating conditions obtained from the developed finite element model are compared with analytical model results, and further model improvements are discussed.